How I'm Wearing Cropped Pants Even Though It's Freezing Out

Sometimes, fashion and the real world don't fit together as well as we'd like. For instance, I want these Stella McCartney starry platform loafers (or something similar at a much lesser price point) soooo bad, but I know I would trip and fall at least five times on my way to the train. My Baby Spice dream closet will have to wait. Similarly, when I need a midweek pick-me-up, I’d like to wear this to work:

They are everywhere, offering us a less dramatic option to last spring’s culotte explosion. The two pairs I’ve caved on are both from J.Crew.

Meet the Teddie, a slightly flared fit that’s more fun than my other work pants, and the Rayner, a wide-leg crop that makes me look very IDGAF in a cool, relaxed way (but are as comfortable as any sweatpants-and-UGGS combo).

While I’m super-happy having these in my closet, I haven’t worn either yet. Unfortunately, I live in NYC where it is currently freezing. As I write this, it is 31° and flurrying out. This is no time for exposed ankles.

I don't expect all fashion to be practical, but I do expect my wardrobe to be — for the most part. So let’s talk about today's It pant, the crop, and how to wear it when it's freezing out (as in now until April).

Let your statement boots shine.

This is the easiest way to keep your ankles warm without overthinking your outfit. Sock or mid-calf booties are a great way to show off your shiniest pair of boots and achieve a leggier look. If I weren’t broke from buying all the cropped pants, I’d get these.

It's OK to show some ankle — just be sure to balance it out with an oversized topper.

Contrasting a flash of bare skin with a super cozy coat or scarf looks surprisingly polished, and can (sort of) serve a practical purpose. Overcompensating on top won’t keep your feet any warmer, but it will create a visual and mental balance that might make the cold seem a little less intense. Pro tip: pack an extra pair of socks just in case.

Break out your chunkiest, coziest socks.

This Miu Miu look is too crazy for me, personally, but those socks got me thinking.

Finally, an excuse to show off my bright red, nubby knit socks outside of my apartment!

Put those over-the-knee boots to work.

Wide leg crops aren’t only cold because of the short length; the loose fit guarantees that the freezing wind will blow straight up your leg the second you step outside. The fix? Your knee boots aren’t just for skinny jeans anymore.

Experiment with boot lengths and styles to find the most flattering fit. So far I’ve found this works better with a heel and slight flare over a flat and wide leg combo, but it depends on the person.

High-top sneakers might be too much for this look, but a classic low with a subtle sock isn't.

If this look scares you because of its similarity to Urkel’s favorite outfit, that’s understandable, but I’m convinced we can break this stereotype.

Pick your socks based on their color and length, opting for a smooth knit and a color that’s similar to your pants to continue the line. Steer clear of purely athletic sneakers and try out a classic or skate-inspired silhouette.

Ribbons have popped up all over the runways recently, reminding me just how fun it was to coordinate grosgrain into my third-grade outfits. But as an adult, this trend seemed too DIY.

That changed after seeing how the team at Dior expertly wrapped wide ribbons around ankles. Now I have to try this for myself. It’s a style dare moment, but if it makes me feel more like Madame Pompadour, why not?